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Details

Stereochemistry ACHIRAL
Molecular Formula C5H9N3
Molecular Weight 111.1451
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HISTAMINE

SMILES

NCCC1=CNC=N1

InChI

InChIKey=NTYJJOPFIAHURM-UHFFFAOYSA-N
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)

HIDE SMILES / InChI

Description

Histamine is a depressor amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and a centrally acting neurotransmitter. Phosphate salt of jistamine was used as a diagnostic aid for evaluation of gastric acid secretory function. In addition, this compound is used as a positive control in evaluation of allergenic (immediate hypersensitivity or "Type I") skin testing. In addition, histamine is being studied for treatment of multiple sclerosis. It was approved, that histamine physiological functions are mediated by four 7-transmembrane G protein-coupled receptors (H1R, H2R, H3R, H4R) that are all targets of pharmacological intervention. The receptors display molecular heterogeneity and constitutive activity. H1R antagonists are long known antiallergic and sedating drugs, whereas the H2R led to the development of H2R-antagonists that revolutionized stomach ulcer treatment. The H3R is an auto receptor and heteroreceptor providing negative feedback on histaminergic and inhibition on other neurons. The H4R occurs on immuncompetent cells and the development of anti-inflammatory drugs is anticipated.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
HISTAMINE PHOSPHATE
Primary
Diagnostic
HISTAMINE PHOSPHATE
PubMed

PubMed

TitleDatePubMed
The physiology of brain histamine.
2001 Apr
Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial.
2001 Feb
No correlation between wine intolerance and histamine content of wine.
2001 Feb
Histamine alters gene expression in cultured human nasal epithelial cells.
2001 Feb
Acquisition and alteration of adhesion molecules during cultured human mast cell differentiation.
2001 Feb
IL-4 production by human basophils found in the lung following segmental allergen challenge.
2001 Feb
Histamine prevents polyamine accumulation in mouse C57.1 mast cell cultures.
2001 Feb
Double-blind, placebo-controlled food challenge with apple.
2001 Feb
Inhibitory action of water soluble fraction of Terminalia chebula on systemic and local anaphylaxis.
2001 Feb
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.
2001 Feb
Nedocromil sodium inhibits histamine-induced itch and flare in human skin.
2001 Feb
A human tissue-engineered vascular media: a new model for pharmacological studies of contractile responses.
2001 Feb
IL-13 overexpression predisposes to anaphylaxis following antigen sensitization.
2001 Feb 15
Selective down-regulation of high-affinity IgE receptor (FcepsilonRI) alpha-chain messenger RNA among transcriptome in cord blood-derived versus adult peripheral blood-derived cultured human mast cells.
2001 Feb 15
The activation of synovial mast cells: modulation of histamine release by tryptase and chymase and their inhibitors.
2001 Feb 2
Involvement of central histaminergic neurons in polypnea induced by hyperthermia in rabbits.
2001 Feb 2
Mesenchymal transcription factor Fkh6 is essential for the development and differentiation of parietal cells.
2001 Feb 2
Comparison of montelukast and fexofenadine for chronic idiopathic urticaria.
2001 Jan
Preclinical profile of the monodisperse iodinated macromolecular blood pool agent P743.
2001 Jan
The dyspepsia alphabet: DU, GU, GERD, NERD, NUD/FD and UD.
2001 Jan
Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis.
2001 Jan
Combination therapy with anti-mediator drugs in allergic disease.
2001 Jan
Urticaria induced by cetirizine.
2001 Jan
Interleukin-4-positive mast cells are highly associated with the extent of immediate allergic wheal reaction in the skin.
2001 Jan
A randomized, double-blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine-induced cutaneous responses in healthy adult volunteers.
2001 Jan
Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma.
2001 Jan
The treatment of rhinovirus infections: progress and potential.
2001 Jan
Effect of acute metabolic acid/base shifts on the human airway calibre.
2001 Jan
Effects of BP 2-94, a selective H(3)-receptor agonist, on blood flow and vascular permeability of the rat mandibular incisor pulp.
2001 Jan
Mediator involvement in antigen-induced bronchospasm and microvascular leakage in the airways of ovalbumin sensitized Brown Norway rats.
2001 Jan
Inhibition by glucocorticoids of the mast cell-dependent weal and flare response in human skin in vivo.
2001 Jan
Effect of the long-acting tachykinin NK(1) receptor antagonist MEN 11467 on tracheal mucus secretion in allergic ferrets.
2001 Jan
Antihistamines.
2001 Jan
Medical therapy for gastroesophageal reflux disease.
2001 Jan
Effects of cetirizine and epinastine on the skin response to histamine iontophoresis.
2001 Jan
Characterization of itch-associated responses of NC mice with mite-induced chronic dermatitis.
2001 Jan
Management of severe gastroesophageal reflux disease.
2001 Jan
Regulatory effect of histamine H1 receptor antagonist on the expression of messenger RNA encoding CC chemokines in the human nasal mucosa.
2001 Jan
Role of kinins in seasonal allergic rhinitis: icatibant, a bradykinin B2 receptor antagonist, abolishes the hyperresponsiveness and nasal eosinophilia induced by antigen.
2001 Jan
Luminal Nalpha-methyl histamine stimulates gastric acid secretion in duodenal ulcer patients via releasing gastrin.
2001 Jan 26
Questions regarding future research on aspirin and the gastrointestinal tract.
2001 Jan 8
Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity.
2001 Jan 8
Approaches to healing and prophylaxis of nonsteroidal anti-inflammatory drug-associated ulcers.
2001 Jan 8
CLA reduces antigen-induced histamine and PGE(2) release from sensitized guinea pig tracheae.
2001 Mar
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.
2001 Mar
Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin.
2001 Mar
Complement-dependent immune complex-induced bronchial inflammation and hyperreactivity.
2001 Mar
Decreased brain histamine-releasing factor protein in patients with Down syndrome and Alzheimer's disease.
2001 Mar 2
Correlation between neutral endopetidase (NEP) 3.4.24.11 in serum and the degree of the bronchial hyperreactivity.
2001 Mar 2
Extracts of ECL-cell granules/vesicles and of isolated ECL cells from rat oxyntic mucosa evoke a Ca2+ second messenger response in osteoblastic cells.
2001 Mar 2
Patents

Sample Use Guides

In Vivo Use Guide
The skin in the test area should be cleansed with alcohol and air dried. The histamine control skin test solution should be placed at the same site with the other skin test antigens, either on the patient's back or on the volar surface of the forearm. The patient should be placed in a comfortable position before the testing is begun. For the prick test, a sharp needle is used to puncture the skin, but not to draw blood. If the scratch test is used, carefully break or scratch the skin with a sterile scarifier. Do not draw blood. Each scratch should be about 2 mm - 4 mm in length. A small drop of the histamine base 1 mg/mL (Histamine Phosphate 2.75 mg/mL) is placed on the abraded skin site no closer than 4 or 5 cm from an adjacent test site. Some physicians prefer to place the solution on the test area and then prick through the drop with a sharp needle.
Route of Administration: Parenteral
In Vitro Use Guide
Histamine prevented monocytic apoptosis induced by serum deprivation, CD95/Fas ligation, or dexamethasone in a dose- and time-dependent fashion. The inhibitory effects of histamine on monocytic apoptosis were blocked by an H2R antagonist, and mimicked by an H2R agonist. Histamine also up-regulated the expression of Bcl-2 and Mcl-1, and inhibited the activation of caspase-3. The culture supernatants from histamine-treated monocytes inhibited monocytic apoptosis, which was partly reversed by the removal of IL-10. Monocytes cultured with anti-IL-10 mAb and histamine did not exhibit an inhibitory effect on apoptosis. The histamine-induced anti-apoptotic effect was attenuated when monocytes were cultured in the presence of a cAMP inhibitor.
Name Type Language
HISTAMINE
HSDB   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ERGOTIDINE
Common Name English
ERGAMINE
Common Name English
NSC-33792
Code English
HISTAMINE [WHO-DD]
Common Name English
HISTAMINE [MI]
Common Name English
5-IMIDAZOLEETHYLAMINE
Systematic Name English
HISTAMINE [MART.]
Common Name English
1H-IMIDAZOLE-4-ETHANAMINE
Systematic Name English
HISTAMINE [VANDF]
Common Name English
.BETA.-AMINOETHYLGLYOXALINE
Common Name English
4-IMIDAZOLEETHYLAMINE
Systematic Name English
.BETA.-AMINOETHYLIMIDAZOLE
Systematic Name English
2-(4-IMIDAZOLYL)ETHYLAMINE
Systematic Name English
HISTAMINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C687
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
FDA ORPHAN DRUG 127199
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
FDA ORPHAN DRUG 127399
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
WHO-ATC L03AX14
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
NCI_THESAURUS C2139
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C73238
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-100-6
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
CAS
51-45-6
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
WIKIPEDIA
HISTAMINE
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
MESH
D006632
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
MERCK INDEX
M6026
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY Merck Index
PUBCHEM
774
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
EPA CompTox
51-45-6
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
HSDB
51-45-6
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY
RXCUI
5333
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY RxNorm
EVMPD
SUB14107MIG
Created by admin on Tue Oct 22 00:40:44 UTC 2019 , Edited by admin on Tue Oct 22 00:40:44 UTC 2019
PRIMARY